反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20]>CN1C(=O)CCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:2]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:4][C:3]=2[C:19]([F:22])([F:21])[F:20])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1参加物
反応条件
- 温度
- 120 °C
実験手順
To a mixture of 1-chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene (1.5 g, 4.5 mmol) and cyclohexylzinc bromide THF solution (0.5 M, 27 mL) in NMP (30 mL) is added bis(tri-t-butylphosphine)palladium(0) (115 mg, 0.225 mmol). The mixture is purged with N2 for 5 min, followed by heating at 120° C. 12 h under N2. After cooling to room temperature, the reaction is quenched by the addition of H2O (100 mL) and aqueous HCl (1N, 20 mL). The mixture is extracted with EtOAc (3×40 mL). The combined organic phases are washed with saturated aqueous NaHCO3, saturated aqueous NaCl, and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (5% EtOAc in hexanes) to give 1-cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene as a colorless oil.
後処理
- customThe mixture is purged with N2 for 5 min
- custom12 h
- temperatureAfter cooling to room temperature
- customthe reaction is quenched by the addition of H2O (100 mL) and aqueous HCl (1N, 20 mL)
- extractionThe mixture is extracted with EtOAc (3×40 mL)
- washThe combined organic phases are washed with saturated aqueous NaHCO3, saturated aqueous NaCl
- dry with materialdried over Na2SO4
- concentrationAfter concentration
- customthe residue is purified by silica gel chromatography (5% EtOAc in hexanes)
出典と根拠
- ORDレコード
- ord-085e122cf6734cf3a6b765484238f086
- 出典データセット
- uspto-grants-2006_06
- 特許番号
- US07060697B2
関連ノート
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